673-31-4

Basic information

• Product Name: Phenprobamate
• Synonyms: Actozin;PHENPROBAMATE;1-Carbamoyloxy-3-phenylpropane;1-Propanol, 3-phenyl-, carbamate;3-phenyl-1-propanocarbamate;3-Phenyl-1-propanol carbamate;3-phenyl-1-propanolcarbamate;3-Phenylpropyl carbamate
• CAS NO: 673-31-4
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• EINECS: 211-606-1
• Product Categories: Anesthetic Agents
• Mol File: 673-31-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 101-104°
• Boiling Point: 311.75°C (rough estimate)
• Flash Point: 183.1oC
• Appearance: /
• Density: 1.1248 (rough estimate)
• Vapor Pressure: 4.69E-05mmHg at 25°C
• Refractive Index: 1.5710 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 13.47±0.50(Predicted)
• CAS DataBase Reference: Phenprobamate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenprobamate(673-31-4)
• EPA Substance Registry System: Phenprobamate(673-31-4)

Safety Data

• Hazardous Substances Data: 673-31-4(Hazardous Substances Data)

Usage

Chemical Properties

White shiny crystalline powder. Melting point 101-104°C, soluble in ethanol, chloroform, propylene glycol and ethylenediamine, slightly soluble in ether, almost insoluble in water. Odorless, slightly bitter taste, slightly numb.

Uses

Phenprobamate (3-phenylpropylcarbamate) is a centrally acting muscle relaxant with mild sedative and anticonvulsant effects. Muscle relaxants can enhance and prolong the effect of narcotic drugs and enable to obtain same effect with a smaller amount of alcohol or illicit substance.

Definition

ChEBI: Phenprobamate is a member of benzenes.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Used as a tranquilizer and muscle relaxant. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES and ESTERS

InChI:InChI=1/C10H13NO2/c11-10(12)13-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H2,11,12)

Synthetic route

3-Phenyl-1-propanol (122-97-4) + carbamic acid phenyl ester (622-46-8) → phenprobamate (673-31-4)

Conditions	Yield
With di-n-butyltin maleate In toluene at 90℃; for 4h;	99%

3-Phenyl-1-propanol (122-97-4) + methyl carbamate (598-55-0) → phenprobamate (673-31-4)

Conditions	Yield
With di-n-butyltin maleate In toluene for 3h; Reflux;	98%

3-Phenyl-1-propanol (122-97-4) + sodium cyanide (143-33-9) → phenprobamate (673-31-4)

Conditions	Yield
With trifluoroacetic acid

C12H12Cl3NO3 → phenprobamate (673-31-4)

Conditions	Yield
With methanol; potassium carbonate In 1,2-dichloro-ethane Inert atmosphere;

3-Phenyl-1-propanol (122-97-4) → phenprobamate (673-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,2-dichloro-ethane / 5 h / 0 °C / Inert atmosphere 2: methanol; potassium carbonate / 1,2-dichloro-ethane / Inert atmosphere View Scheme

3-phenylpropyl hydroxycarbamate → phenprobamate (673-31-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / diethyl ether / 12 h / 0 - 20 °C 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate / 12 h / 25 °C / Inert atmosphere; Irradiation View Scheme

3-phenylpropyl [{3,5-bis(trifluoromethyl)benzoyl}oxy]carbamate → phenprobamate (673-31-4)

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate at 25℃; for 12h; Inert atmosphere; Irradiation;	30 %Spectr.

phenprobamate (673-31-4) + pinacol vinylboronate (75927-49-0) → (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene (1000376-26-0)

Conditions	Yield
Stage #1: phenprobamate With (2-methylpropyl)lithium In diethyl ether; hexane; cyclohexane at -78℃; for 5h; Stage #2: pinacol vinylboronate In diethyl ether; hexane; cyclohexane at -78℃; for 1h; Stage #3: With magnesium dibromide etherate In diethyl ether; hexane; cyclohexane at 20℃; for 16h; Reflux; enantioselective reaction;	79%

phenprobamate (673-31-4) + 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane (83947-58-4) → (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene (1428538-05-9)

Conditions	Yield
Stage #1: phenprobamate With (2-methylpropyl)lithium In diethyl ether; hexane; cyclohexane at -78℃; for 5h; Stage #2: 4,4,5,5-tetramethyl-2-[(1E)-prop-1-en-1-yl]-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78℃; for 1h; Stage #3: With magnesium dibromide etherate In diethyl ether; hexane; cyclohexane at 20℃; for 16h; Reflux; enantioselective reaction;	77%

phenprobamate (673-31-4) → (+/-)-4-phenyl-1,3-oxazinan-2-one

Conditions	Yield
With iodosylbenzene; (±)-trans-N,N′-1,2-cyclohexylenebis(4-nitrobenzylideneamine); tetrakis(acetonitrile)copper(I) hexafluorophosphate In acetonitrile at 45℃; Molecular sieve; Inert atmosphere;	54%

phenprobamate (673-31-4) + 3-trifluoromethylphenyl sulfinic acid sodium salt (118849-61-9) + Glyoxilic acid (298-12-4) → (3-Phenyl-propoxycarbonylamino)-(3-trifluoromethyl-benzenesulfonyl)-acetic acid (41142-04-5)

Conditions	Yield
(i) aq. HCO2H, (ii) /BRN= 1959273/; Multistep reaction;

phenprobamate (673-31-4) + Sodium; 2-chloro-5-trifluoromethyl-benzenesulfinate + Glyoxilic acid (298-12-4) → (2-Chloro-5-trifluoromethyl-benzenesulfonyl)-(3-phenyl-propoxycarbonylamino)-acetic acid (41142-18-1)

Conditions	Yield
(i) H2O, (ii) /BRN= 6307616/, HCO2H; Multistep reaction;

(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester + phenprobamate (673-31-4) → C17H25BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester In diethyl ether; hexane; cyclohexane at -78 - 20℃;

(E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester + phenprobamate (673-31-4) → C17H25BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (E)-1-propenylboronic acid 2,2-dimethyl-1,3-propanediol ester In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane → C20H29B

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane → C20H29B

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-prop-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane → C23H35B

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane → C23H35B

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: 9-((E)-hex-1-enyl)-9-borabicyclo[3.3.1]nonane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane → C23H37BOSi

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane → C23H37BOSi

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: ((E)-3-(9-borabicyclo[3.3.1]nonan-9-yl)allyloxy)trimethylsilane In diethyl ether; hexane; cyclohexane at -78℃;

phenprobamate (673-31-4) + B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane (1218988-11-4) → C20H31BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane (1218988-11-4) → C20H31BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: B-2-(E)-(hex-1-en-1-yl)-5,5-dimethyl-1,3,2-dioxaborinane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane (83947-59-5) → C18H27BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane (83947-59-5) → C18H27BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-4,4,5,5-tetramethyl-2-(prop-1-en-1-yl)-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (91083-23-7) → C21H33BO2

Conditions	Yield
Stage #1: phenprobamate With sec.-butyllithium; (-)-sparteine In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) + (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (91083-23-7) → C21H33BO2

Conditions	Yield
Stage #1: phenprobamate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane; cyclohexane at -78℃; Stage #2: (Z)-2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; hexane; cyclohexane at -78 - 20℃;

phenprobamate (673-31-4) → (1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol (1218988-28-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C 2.3: 16 h / -78 - 20 °C View Scheme

phenprobamate (673-31-4) → (1R,2R,3Z)-2-methyl-1,6-diphenylhex-3-en-1-ol (1218988-13-6) + (1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol (1218988-28-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: tetrahydrofuran / 96 h / 20 °C View Scheme

phenprobamate (673-31-4) → ((3R)-5-phenylpent-1-en-3-yl)trifluoroborate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: L-Tartaric acid / acetonitrile; water; tetrahydrofuran; methanol / 20 °C View Scheme

phenprobamate (673-31-4) → (1R,3Z)-1,6-diphenylhex-3-en-1-ol (1428537-74-9) + (1S,3E)-1,6-diphenylhex-3-en-1-ol (1428537-73-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: tetrahydrofuran / 96 h / 20 °C View Scheme

phenprobamate (673-31-4) → (1S,3E)-1,6-diphenylhex-3-en-1-ol (1428537-73-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: (2-methylpropyl)lithium / hexane; cyclohexane; diethyl ether / 5 h / -78 °C 1.2: 1 h / -78 °C 1.3: 16 h / 20 °C / Reflux 2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 2.2: 0.5 h / -78 °C 2.3: -78 - 20 °C View Scheme

Upstream product

• 122-97-4 3-Phenyl-1-propanol 
• 143-33-9 sodium cyanide 
• 598-55-0 methyl carbamate 
• 622-46-8 carbamic acid phenyl ester 

Downstream Products

• 1218988-28-3 (1S,2S,3E)-2-methyl-1,6-diphenylhex-3-en-1-ol 
• 1218988-13-6 (1R,2R,3Z)-2-methyl-1,6-diphenylhex-3-en-1-ol 
• 1428537-74-9 (1R,3Z)-1,6-diphenylhex-3-en-1-ol 
• 1428537-73-8 (1S,3E)-1,6-diphenylhex-3-en-1-ol 
• 1000376-26-0 (3R)-3-(4',4',5',5'-tetramethyl-1',3',2’-dioxaborolanyl)-5-phenylpent-1-ene 
• 1428538-05-9 (2E,4R)-4-(4’,4’,5’,5’-tetramethyl-1’,3’,2’-dioxaborolanyl)-6-phenylhex-2-ene 
• 41142-18-1 (2-Chloro-5-trifluoromethyl-benzenesulfonyl)-(3-phenyl-propoxycarbonylamino)-acetic acid 
• 41142-04-5 (3-Phenyl-propoxycarbonylamino)-(3-trifluoromethyl-benzenesulfonyl)-acetic acid 

Relevant articles and documents

Further development of the tin-catalyzed transcarbamoylation reaction

Studies carried out to further develop tin-catalyzed trans-carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate was found to be an economical carabamoyl donor in tin-catalyzed transcarbamoylation, which showed broad functional group tolerance and allowed a streamlined workup procedure. Finally, a unique synthetic method was developed for the preparation of carbamate-tethered terpene glycoconjugates.

Copper-catalyzed intramolecular C-H amination

The amino-functionalization of tertiary, secondary and benzylic C-H bonds of tethered carbamates and sulfamates by iodosobenzene is catalyzed by Cu I-diimine complexes in moderate to good yield. Employing homochiral imine-Cucatalysts affords oxazolidinones and oxathiazinanes with modest enantioselectivity.

Quantitative structure-activity relationships of anticonvulsant aralkyl and alkyl carbamates

-